Ozone → (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone

Participants

Reaction Steps

An ozone stream (3 g ozone/hour) was conducted for 80 minutes while stirring through a solution, cooled to -70°, of 15.2 g of (RS)-2-(2-buten-1-yl)-6-methoxy-1-indanone in 250 ml of anhydrous dichloromethane and 50 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 7.75 ml of dimethyl sulfide, the mixture was stirred at room temperature for 15 hours. The reaction mixture was evaporated in a vacuum, the residue was treated with 250 ml of dichloromethane and, after the addition of 25 ml of water and 25 ml of trifluoroacetic acid, stirred at room temperature for 3 hours. The mixture was subsequently poured into 150 ml of water and neutralized while stirring by the spatula-wise addition of sodium hydrogen carbonate. An additional 100 ml of water were added, the phases were separated and the aqueous phase was extracted twice with 150 ml of dichloromethane each time. The combined organic phases were dried over magnesium sulfate, concentrated in a vacuum and the crude product obtained was crystallized from diethyl ether/hexane. 12 g (83%) of (RS)-2-(2-oxoethyl)-6-methoxy-1-indanone were obtained as a light yellow solid with m.p. 59°.

Provenance & Evidence